


She Who Holds the Key

by winchestershiresauce



Category: Supernatural
Genre: Blow Jobs, Chastity Device, Cock Cages, Cunnilingus, Dean Winchester Gives Oral Sex, F/M, Multiple Orgasms, NSFW, Oral Sex, Plot What Plot/Porn Without Plot, Reader-Insert, Sex Toys, Shameless Smut, Smut, Sub!Dean, Teasing, brief appearance by Sam Winchester - Freeform, reader gives oral sex, torturous teasing
Language: English
Status: Completed
Published: 2020-10-20
Updated: 2020-10-20
Packaged: 2021-03-08 22:33:53
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,999
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27123896
Author URL: https://archiveofourown.org/users/winchestershiresauce/pseuds/winchestershiresauce
Summary: Dean and Y/N incorporate a chastity cage for the first time and sexy fun times abound.
Relationships: Dean & Reader, Dean Winchester & You, Dean Winchester/Reader, Dean Winchester/You
Kudos: 26





	She Who Holds the Key

Not knowing when they’d finally have the bunker to themselves, Y/N and Dean had been planning for weeks. They’d researched different products, watched videos, read everything they could find, and finally bought and stashed the goods. When he’d discovered their sexual chemistry, Dean couldn’t believe his luck. They’d been friends and occasional hunting partners for a while, but the sex was downright addictive. Never before had he been with someone who understood him on such an intimate level and, since they’d had the hunters-don’t-have-real-relationships talk a thousand times, he knew they were on the same page. Finally, Dean felt like he could truly be himself around someone. There was one kink that Dean had fantasized about that he had never shared with a single soul. Not until Y/N, that is.

When Sam came into the library to announce that Jody was requesting his help on a small case outside Sioux Falls, Y/N and Dean shared an excited glance before fixing their faces with a more neutral visage. 

“Sounds good,” Dean replied, trying to seem nonchalant, “Do you need backup?” He looked over at Y/N and back up at Sam.

“I don’t think so. It seems like a pretty open-and-shut case, but she wanted an extra body just in case anything went sideways,” Sam shrugged. “You guys’ll be okay by yourselves for a couple days, right?” He looked right at Y/N and she smirked.

“I’m sure we’ll find some way to keep ourselves occupied,” she replied. Pink crept onto Dean’s cheeks as he allowed himself to get excited. They were finally doing this.

\--

At 7:30 on the dot, Dean walked into the Dean Cave to find Y/N on one of the La-Z-Boys in front of the tv, flipping through the seemingly endless choices that Netflix had to offer. He came in casually, plopping down on the other recliner. “Are we watching a movie?” he asked, nervously.

“Yeah, I figured we’d just hang out for a while,” she answered, her eyes not leaving the tv in front of her. He nodded. She selected a movie they’d both seen before and set the remote on the table between them. “You wearing it?” she questioned quietly, still staring at the screen. The corner of his mouth pulled into a smirk. When he didn’t immediately answer, she looked over at him, noticing how his green eyes sparkled with the reflection of the tv. Her smirk mirrored his and she reached over to set her hand on his. “How’s it fit?”

“Snug as a motherfucker!” He shifted in his seat and she couldn’t help the laugh that bubbled past her lips. “It’s okay, though. I think I like it,” he added.

“Good,” she responded, “Use your safewords if you need them.” He gave her a thumbs up. “How about you go get us some popcorn?” She looked up at him through thick lashes and he rolled his eyes.

“Butter?”

“Of course.” He got up to fetch the popcorn and she laid back in her seat, making herself comfortable. “Oh! And Dean?” He popped his head back in the room. “I’ll take the key.” 

About halfway through the movie, Y/N looked over at Dean. For a few moments, she watched his firm chest rise and fall rhythmically with his breath. She admired the view, noticing the way the sleeves of his t-shirt pulled snug across his solid biceps. She followed the vein that wrapped around his elbow, unable to help thinking about how those strong arms felt around her. Her eyes moved to his hand fidgeting with the fabric of the chair. She flinched when he suddenly cleared his throat. She looked up at him and knew she’d been caught staring. After glancing away sheepishly for the briefest of moments, she stood and walked over toward him. His eyes followed her and his mouth dropped open a bit as she settled herself into his lap.

“Hi.” She gently ran her fingertips across his scalp and he swallowed hard.

“Hi, yourself.” His voice was strangled. She slid one hand down his chest and abdomen, stopping at his waistband. He stared into her eyes, waiting to see what her next move would be. 

“Can I?” she asked. He didn’t think he could answer without his voice cracking, so he nodded. She cupped her hand between his legs and bit her lip when she felt the hard plastic under his flannel pajama pants. Out of instinct more than anything, he pushed his hips up against her hand. He growled in frustration, feeling the rush of blood to his cock but instead of hardening against her, he strained against the cage containing his manhood. He threw his head back and she pressed her lips against the sensitive skin of his throat. He grabbed her head in his hands and pulled her mouth to his in a bruising kiss. She ran her tongue along his bottom lip, shoving it into his mouth when he opened up for her. He thread his fingers through her hair, and she pressed herself down against the hardness of the plastic between his legs. When she moved at just the right angle, it made contact with her clit and they both gasped: her with pleasure, and him with a combination of lust, need, and frustration.

He moved his hands to cup the soft globes of her ass, pushing her to grind down harder against him. She rolled her hips in his lap, rubbing herself against the solid bulge in his pants. Her arousal pooled between her legs, drenching her panties and threatening to soak through her jeans. When she pulled up for air, panting, Dean mouthed at her exposed collarbone before he pulled back to lift her shirt over her head. As he undid the clasps of her bra and allowed her breasts to fall free, she ground down on him hard, but she wanted more.

“I need you, Dean,” she whined. It was all the prompting he needed to hold her against him as he stood. She stood up with him and pulled his lips to hers again. His fingers made quick work of the button on her jeans and he thrust his hand between her skin and her panties. He slid his middle finger against her slit and immediately felt how soaked she was.

“Fuck, Y/N. So wet,” he groaned, dipping the pad of his finger between her folds. He pressed against her sensitive clit and she gasped.

“Fuck. Dean, I- I need- your mouth,” she panted, “Now.” His cock was throbbing as he yanked her jeans and panties down off her hips. He pushed her back onto the chair and dropped to his knees in front of her. He pressed a kiss to her outer folds and her head lolled back against the chair. He pulled her to the edge of the seat and draped one of her legs over his shoulder. Using his fingers to open her up, he flattened his tongue and licked a line from opening to clit. She lifted her hips up toward the warmth of his mouth as he wrapped his lips around her swollen bundle of nerves. With one arm across her waist, he held her in place as he flicked the tip of his tongue over her aching bud. She felt herself getting close to the edge as he slipped a single finger inside of her waiting entrance. He continued his ministrations on her clit as he worked a second finger inside her. When the tip of his calloused middle finger pressed against her sweet spot, she tumbled over the edge, spasming around his digits. As the spasms slowed, Dean looked up at her flushed face. He wasn’t sure he’d ever been so turned on in his life and yet the cage wouldn’t allow him to get fully hard.

“Take me to bed, Dean,” she croaked. He was more than happy to oblige, scooping her up into his arms and carrying her toward his bedroom. As he moved to set her on the bed, she dropped her legs to the floor and stood. With one hand, her fingers tangled in his soft golden brown locks as she looked up into his eyes. She slipped her other hand under his waistband, reaching around to pinch his firm cheeks. He growled and pulled her bottom lip between his teeth. She dropped her hand from his hair and slid his pants off his sharp hips.

She sat on the edge of the bed and her eyes darkened with the sight in front of her. Wrapped around his member was a black plastic cage. A thick ring wrapped behind his sac and around the top of his cock, flush against his flesh. His length itself was trapped in the actual cage, precum drooling out of the opening at the tip. Y/N bit her lip and squeezed her thighs together, casually wondering if he might be wetter than she was. She looked up at him and he cupped her cheek in his sweaty palm. He let out a low groan as the cool air nipped at his exposed-yet-contained package. She nuzzled her face into his hand as she ran her fingers across the exposed skin around his cage. A shiver ran up his spine at the light touch and he squeezed his eyes closed. He couldn’t find words to describe how simultaneously turned on and frustrated he was at the scene. His leaking tip was dark red, aching to be allowed to reach its full length and hardness. His mind was so engulfed with the strain against his prison that he didn’t feel Y/N move until the light tickle of her breath ghosted across the hot flesh beneath the cage. 

She smiled to herself, feeling his whole body tense as she ran her tongue up the length of the cage. He could feel the warmth of her mouth and the tip of her tongue as it slipped between the spaces in the plastic, and he wanted nothing more than to feel her lips wrapped tightly around him. He knew, however, that in his current predicament, it wouldn’t feel like he wanted it to. As if reading his mind, she wrapped her lips around the plastic encasing his cock. A strangled moan escaped him as his length twitched inside its confines, trying with all its might to swell into the hot, wet cavern of her mouth. She pulled back and grinned up at him, strings of his precum dripping from her lips. 

Dean’s pupils were blown so big that his eyes looked black as she pulled him down onto the bed with her. He crawled over her, covering her body with his own. Their mouths met with hungry, open-mouthed kisses as her arms wrapped around his shoulders and pulled him tight to her. When his caged cock hit the warm wetness of her slick, his breath stopped and his body stilled. 

“You okay?” she asked as he squeezed his eyes closed. He didn’t immediately respond, so she continued, “Hey, what color are you?” 

He dropped his head onto her shoulder and grumbled, “Green. I’m green,” into her bare skin. She grabbed a fistful of his hair and pulled him back so she could look at his face. He looked downright drunk with pleasure. “Just… when my dick slid between your lips, it expected to slide home, but I can only get about a quarter-chub going so I thought I might die for a second,” he laughed. She barely had time to grin before he was kissing her again. Despite the overwhelming sensation, he dragged his caged length through her folds. Her wetness combined with his precum left them both so slick and ready that he slid through her folds with such little effort that he flinched when her legs wrapped tight around his hips. The hard, now-warm tip of the cage rubbed against her clit and she was desperate.

“Dean, I want you to fuck me,” she cried and it was like the sound of a hallelujah chorus to his ears.

He pulled back and looked down at her with a dopey smile, “Fuck, I thought you’d never ask. Where’s the key?” She pursed her lips and his eyes somehow grew even darker.

“Not with  _ your _ dick, Dean,” she replied and he cocked an eyebrow, unsure what she meant. “With  _ mine _ .” His eyes widened dramatically.

“What?” he choked.

“My dildo, Dean. The big one I keep in my nightstand.” In a daze, he nodded and stood next to the bed. He looked down at her for a moment, splayed out on his bed, hair a mess, face flushed red, and a pussy so soaked that there was a wet spot on the sheet under her, and he couldn’t believe that this whole sexy display was for him. “Today, maybe?” she teased.

“Right.” He nodded and walked out of the room. She laid there waiting, biting back a light laugh at the delicious torture she was inflicting on him. If they hadn’t already discussed just how desperate he wanted her to make him, she would’ve felt a little bad. 

He came back into the room, large girthy dildo in hand. She smiled sweetly at him as he climbed back onto the bed. He was just  _ aching _ to be inside her, but he knew he wouldn’t be. Not then, anyway. He took the silicone phallus and slid it through her wet, swollen lips.

“Fuck me, Dean!” she squealed and he plunged the toy deep into her cunt. She cried out, writhing with pleasure, as he found a rough, quick rhythm. With one leg on the floor and the other between her legs, his cock drooled all over her thigh, wanting so desperately to be what was fucking into her. The squelching sound of her pussy being pounded into with the silicone was so obscene, and so fucking beautiful that it made his head spin. Knowing that he was doing that to her, making her make those sounds, but not getting to feel her suck him in, not getting the physical pleasure of fucking her, spurred him on further. With the hand not controlling the movements of the firm fake dick, he pressed his thumb against her clit. The combined force of the toy fucking into her and her hips bucking up to meet each thrust gave the pressure on her clit such a perfect movement that it took no time at all before she was screaming his name as she came. He didn’t slow down his thrusts, rubbing his thumb harder and faster along her clit, and soon she was gushing around the silicone in his hand. If it weren't for the fucking chastity cage, he would have cum right there with her. He knew that even without feeling her warm wetness pulse around him, he wouldn't have been able to hold back. His cock throbbed,  _ ached _ , and leaked so much that he was almost dizzy. 

As she came down from her climax, her shallow breaths began to even out and she wiped a sweaty strand of hair out of her face. She looked up at Dean, unsure what to expect, and he was panting like he’d also just cum. She smiled and sat up.

“I’ll be right back. Don’t go anywhere,” she announced before padding out of the room. She returned quicker than he expected, and he looked up to see her leaning against the doorframe, dangling the key from her finger. She looked to him, expectantly, and he could only nod. “Sit,” she said, pointing to the bed as she approached. He did as he was told. She kneeled on the cold floor in front of him and gently parted his thighs with her hands. His legs quivered at her touch, tense and electric like a live wire inside him. Trying to be as gentle as possible, she carefully clicked the key into the lock and the cage sprung open. She pulled the dripping plastic off of him and dropped it onto the floor next to her. Without any of the tension leaving his muscles, he let out the breath he hadn't realized he'd been holding. His eyes met hers and he wondered whether she could see how he trembled, or maybe he was just wound so tightly that he felt like he was trembling. 

“Still green?” she asked with a smirk, and he let out a breathless laugh.

“Fuck yeah,” he replied. “I'd really love to cum, though.”

“And you deserve to. That was incredible,” she responded, her voice breathy. “Lay back.” He laid back on the bed and she ran her hands up his firm, sweaty thighs. She grinned as he immediately swelled and hardened. “Feel good to be free?” she asked.

As he started to answer, she wrapped her lips around him and sucked him in. He choked on whatever words he was going to say and bucked up into her hot mouth. She bobbed up and down, finding a quick, smooth rhythm, and running her tongue along the sensitive skin on the underside of his crown. He let out a strangled cry and before she knew it, the salty tang of his cum was spurting down her throat. For half a moment, he was embarrassed by how quickly he came, but that thought was immediately overpowered by the intensity of his orgasm. With all the build up and tension and not a modicum of release, he'd exploded, cumming so hard he saw stars. She worked him through the waves of pleasure, swallowing every last drop that he gave her. She was grinning wildly as he grabbed her and pulled her off him. 

“You’re fucking incredible,” he panted. 

“You’re not so bad yourself, Winchester.” She crawled up onto the bed next to him and curled into his side, both of them so spent and satisfied that they weren’t sure when they’d be able to move from that position.


End file.
